


Fill 'Er Up

by Axelex12



Category: Nightwing (Comics), Robin (Comics), Wonder Woman (Comics), Wonder Woman - All Media Types
Genre: Age Difference, Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe - No Powers, Alternate Universe - Restaurant, Boss/Employee Relationship, Cougar - Freeform, Creampie, Cunnilingus, F/M, Flirting, MILFs, Neck Kissing, Nipple Licking, Nipple Play, Office Sex, Older Woman/Younger Man, Simultaneous Orgasm, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-10-03
Updated: 2020-10-03
Packaged: 2021-03-07 17:40:40
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,254
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26791543
Author URL: https://archiveofourown.org/users/Axelex12/pseuds/Axelex12
Summary: Sweet bonus from his busty boss on the last day of work.
Relationships: Diana (Wonder Woman)/Dick Grayson
Comments: 2
Kudos: 13





	Fill 'Er Up

Richard Grayson tossed the empty bag in the garbage can, having filled the windshield wash buckets for the last time. He checked his phone, and saw that he only had five minutes left in his last day.

He took his time walking back from the diesel fuel island, burning up one of those five minutes. Tomorrow, his evening would be free. He wasn't entirely sure what he was going to do with it, truth to be told. He had plans for the weekend, but everyone would be busy on a Thursday night.

There were only a few short weeks of freedom before he headed off to college, so he was going to make the most of them. He knew that much.

Back inside, the place was filled with conversation and laughter, as it usually was. There were larger truck stops, in more convenient locations, but most of the local truckers all stopped at Diana's, and word had spread to long-distance drivers. The kitchen was open 24/7, and the food was good. The bathrooms and showers were clean. The shelves were always well stocked.

If asked, every one of the truckers would have only considered those amenities an afterthought, though. To a man, they were there to see Dinah Lance, Shayera Hol, Helena Bertinelli, or Diana herself. All in their late 30s or early 40s, they were attractive, and flirtatious in the extreme.

Darkhaired Diana Prince was filling coffee cups in the dining area. She was wearing a pleated skirt, which hid her gorgeous ass, but showed off her equally incredible legs. Her low-cut top revealed ample cleavage, and she made sure to bend down frequently while filling cups, so everyone got a good look.

Dick Grayson wasn't excluded from the peeks, or the flirting. No man was. He wasn't immune, either. The last couple of years, the ladies had charmed him into working long shifts, and coming in on his days off many a time. They all had a place in his spank bank of masturbation fantasies.

Diana finished her rounds as Dick walked up to the main counter, where blonde-haired Dinah was entrancing truckers as she rang them up.

"There's our traitor," Diana teased as she approached.

"Leaving us high and dry," Dinah agreed. She addressed the driver at the counter and said, "He's quitting on us, running off to college."

"Must be nuts," the driver said with a grin. "I'd never leave."

Dinah winked and said, "I know you wouldn't, sugar."

"Tried everything to talk him out of it," Diana said, stepping in close and wearing a pout.

Grayson had learned early on that the best way to deal with the flirting was to come right back just as strong. "Everything? I've been hearing this promise about wardrobe malfunctions all this time, and I've never seen it happen."

"Well, maybe you're not paying close enough attention," Diana countered.

Dick grinned and shot back, "Oh, I'm paying attention."

The ladies laughed, as did the truckers in line. Dinah said, "Damn, I'm going to miss this one."

"Won't we all," Shayera agreed. "I should make you stay until the last second, but go ahead back to the office. I'll be back in a minute to cash your last check for you."

"Thanks," Dick Grayson said, and made his way to the employees only door. Once through the stockroom, he followed the long hallway past the break room, bathrooms, service rooms, and back to Diana's office.

About the time he leaned against the wall next to the office door, Diana came through the door on the opposite end of the hall. She called out, "Be right there, honey," before turning into the women's bathroom.

Dick Grayson pulled out his phone and scrolled through some posts until he saw her emerge once more. Diana strutted his way with a smile on her face. Her every move was a performance — and a grand one. Her hips swayed, making her skirt dance, and her hands glided gracefully at her side. She glanced at him and twitched her eyebrows before unlocking the door.

"Have a seat, honey, and I'll get you paid," Diana said as she walked around her desk.

He closed the door — which automatically locked — sat down, and only then noticed that she had something in her hand. Whatever it was, she deposited it in a desk drawer before sitting down as well.

Diana turned on her computer, clicked a few times, and then spun in her chair to access the safe behind her.

"We really are going to miss you," she said while twisting the combination lock dial. "You did such a good job straightening up the back room when you started. Always on time. Never complained." She paused, looked over her shoulder, and added, "Easy on the eyes."

Dick chuckled. "I'll be sure to stop by whenever I'm back home."

"You'd better," Diana said. She reached into the safe, counted out some cash, and then stood. She walked around her desk again, and held out the money with a flourish.

He instantly noticed that there was one more hundred dollar bill than he was expecting as he took the cash. He looked up at her with a question in his eyes.

"A little bonus," Diana explained. "Wish it could be more, but you've earned it."

"Thanks. I really appreciate it," Dick said. It was hardly insignificant, as it was about a quarter of his weekly pay.

"You're welcome. Like I said, you earned it." She then snapped her fingers and said, "You know, I actually do have something else for you."

He couldn't help but grin as she turned and bent over her desk right in front of him. She was getting in one last tease. She slid open her desk drawer while he admired her butt, and the extra inch of leg her rising skirt revealed.

Then it kept rising. Dick stared in stunned amazement as the pleated cloth slid upward. Her rounded ass and bare-shaven pussy were right in front of him, less than a foot away, and they entranced him.

When the surprise wore off and he tore his eyes away from her folds, she was looking back over her shoulder, holding up her skirt with one hand, and the thong she'd retrieved from her desk in the other. She let her panties fall back in the drawer, gave her ass a shake, straightened, and turned around.

"I did promise a wardrobe malfunction," she said. "I keep my promises, honey."

Then she tugged up on her blouse, allowing her big, always braless breasts to tumble free. Though they sagged from their weight and gravity over the years, they were huge and gorgeous. Her nipples and areolas were proportionally large. The points were the size of his pinky to the first knuckle, and the rosy, bumpy halo as big around as a coke can.

His brain began to function again when she hefted one of the globes in the palm of her hand while teasing her stiff nipple with her thumb. He looked up into her eyes — with no small amount of effort. In light of the conversation only minutes before, he said, "I know that I was saying—"

She cut him off with a wave of the hand that wasn't holding her breast. "I'm not trying to make you stay, honey. You need a little time to yourself before you go off to college. I wouldn't do this if you were still working for me. It wouldn't be right. Now that you have your last paycheck, and I'm not your boss anymore..."

It was all having a natural effect on him. He'd actually jerked off to a very similar fantasy only a week or so before. His pants were growing tight, and he fidgeted from the uncomfortable squeeze of the denim. Her eyes dropping to his crotch left little doubt that she'd noticed.

Diana hopped up on the desk, her breasts still bared. She spread her legs, letting him see her pussy in the shadows beneath her skirt.

"The offer's on the table," she said. Then she chuckled and shrugged. "Well, on the desk, I guess."

"You're serious?" he asked, his eyes darting to her tits and pussy of their own volition.

"As a heart attack. You don't know how many times I've diddled myself thinking about it, honey. A couple of times in here, while you were out there working."

The thought of her masturbating to him at work caused his cock to throb hard. She added fuel to that fire by shifting her butt while tugging her skirt upward, until she was once again showing off her pussy in the full light.

"If you want it, don't make me wait, honey," she said. "Or you can go. No hard feelings."

He had a very hard feeling, and it was screaming at him to act. So he did.

"Oh lord, yes," she gasped as he stood and approached.

She popped off the desk, and her hands guided his to her breasts the moment they were in reach. She shuddered as he cupped them, feeling their weight, and then slipped a hand behind his neck, tugging his lips toward them.

Diana whimpered when he sucked her stiff left nipple between his lips. He marveled at how big and hard it was while he sucked. Her hand almost immediately left the back of his neck, and joined the other at his belt.

Dexterous fingers made quick work of his belt, button, and zipper. Grayson sucked hard and squeezed her tits, encouraged by her quiet whimpers of pleasure. She wasted no time pushing down his underwear and taking his cock in hand.

"Oh my lord," she said in a high-pitched whisper as her fingers curled around him. "You're harder than Chinese algebra, honey."

Dick Grayson growled around her nipple and sucked it harder. She was slowly stroking his cock, while rubbing her thumb over the head. It didn't take much of that for a drop of pre-cum to lube up her thumb, increasing the sensation.

"Feel good? You like my big titties?" she asked.

"Mmm hmm," he moaned, not willing to release her nipple to answer.

"You're making my pussy so wet."

Grayson slid his hand down her body and wriggled two fingers between her folds to test that. She wasn't lying. She was soaking wet. Her hand squeezed tight around his erection, she gasped, and stiffened as his fingers probed her.

She shivered once her muscles relaxed, and then whispered in his ear in a husky voice, "I need it, honey. Fuck me. Right now."

Something occurred to him that he hadn't considered in the whirlwind of heat. He let her nipple go and said, "I don't... I don't have a condom."

"I had my tubes tied when I was twenty," she said in a rush of words. "I don't need any kids. What I need is that cock inside me, right now."

Diana pushed down on his pants, but they were too tight for her to make much progress the way he was standing. Dick Grayson straightened, and pushed them down to his knees. She immediately turned around and bent over the desk. He abandoned the thought of kicking off his shoes and taking his pants the rest of the way off when she looked back over her shoulder with her black locks obscuring one eye.

"Fuck me. I want it. I need it, honey," she pleaded.

Fortunately, he didn't need to move forward far, as his pants around his knees made it awkward. He stroked her ass with both hands, and then gave it a light spank.

Diana moaned, but then said, "Don't tease me, honey."

Grayson settled his left hand on her hip, and took his cock in hand with the right. A quick look down was all he needed for the tip to find her folds. She breathed hard as he rubbed the head of his cock up and down, wetting the tip. A single pass was enough to leave him slippery with her juices. Then he pushed.

Diana's eyes widened and her mouth dropped open as he popped into her canal, though only a tiny croak escaped her. Her walls clamped down on him like a vise, preventing him from penetrating more than half his length.

The darkhair sucked in a breath and squeaked, "So big," as he pulled back to thrust again.

"So tight," Grayson said as he pushed a little deeper into her.

Diana's head dropped — her hair dangling — as he filled her with almost his full length before the resistance stopped him again. She grunted, though the sound was curtailed by tightly pursed lips.

He was balls deep inside her on the next stroke, and had to hold back his own groan of pleasure, mindful that someone could be in the break room or bathrooms just down the hall.

Diana grunted and groaned with each slow, powerful thrust, as he opened her up. Dick was surprised by how tight she was, but didn't ponder it. He was enjoying it too much.

After a dozen pumps, she said in a tight, quiet voice, "You're so deep."

He responded, "You feel so good."

Diana bent her arms, and supported herself on one, while the other slipped between her legs. Grayson felt her fingertips brush against him as she rubbed her clit. An almost too-loud gasp escaped her as her pleasure surged.

Dick Grayson maintained his slow pace, reveling in the slippery, satiny embrace of her walls around him. Restrained whimpers escaped her with every thrust, and it was all he could do to remain quiet as well.

"Did... Did you ever imagine this?" she asked.

"Yeah."

She moaned. "Did you come hard?"

A touch of a growl in his voice, he answered, "Fuck yes."

"Fantasizing about fucking you always made me come so hard," she said. "Do you want me to come for you?"

"Oh yeah." To that end, he picked up the pace. He tried to bend over and reach for her tits, but the angle was too awkward.

She was quick to accommodate him. Realizing what he wanted, she straightened her arms again. As soon as he had a double handful of her big, soft tits, she turned her attention back to her clit, allowing him to hold her up.

Grayson pulled her closer, and leaned in to kiss the back of her neck. "I love your fucking tits."

She responded with, "And I love that big, hard, young cock. Give it to me. Faster."

He thrust up into her, and the faint smacks of their bodies colliding joined their bit-off sounds of pleasure.

"Pinch my nipples," she demanded. He did, but she immediately said, "Harder."

Grayson pinched the stiff nubs hard between his finger and thumb. She yelped in her throat, keeping the sound from escaping her lips, though it was still loud. For good measure he squeezed her tits harder as well.

"Yes. Just like that. Don't stop. Fuck me," she said, her voice rising slightly in volume, though still at a whisper.

He felt the first electric itch in the head of his cock not long after, and said, "Come for me."

"Oh yes," she whimpered.

"Do it. Come for me," he said in a growled whisper.

Grayson could hear as well as feel her fingers moving faster over her clit. Her labia made a faint, wet, thrumming sound, mingling with the symphony of their sex. He slammed his cock into her depths as quickly as he could, not willing to let go of her breasts to find a better angle. Diana's hand suddenly snapped to her mouth, stifling an alarmingly loud yelp — followed by a scream.

The darkhaired woman's whole body stiffened in his grasp, her walls clamped down on his cock, and she screamed into her hand as orgasm claimed her. The scream had barely trailed off when she lurched so violently that he slipped free of her pussy. His cock ended up squished against her buttocks as her head lashed forward. She barely caught herself on her elbows, shoving her desk calendar halfway off the desk and askew. Her hand remained over her mouth, quieting the yelps and screams that tried to escape, as the throes of her orgasm rocked her.

Grayson took hold of her hips, grinding his still slick cock against her ass, and watched her claw at the desk. Her body undulated and trembled from the waves of orgasm crashing through her, until they finally began to ebb. Her knuckles rapped on the desk when her hand fell away from her mouth, and she gasped noisily for air.

At the same moment, Grayson had to react fast, because her legs went weak. He barely managed to catch her, keeping her from slumping to the floor.

It was some time before she caught enough breath to groan, and slide an arm beneath her head. "Oh my god," she muttered, her voice garbled because her cheek was pressed so tightly against her arm.

Grayson smiled and caressed her butt — his cock tapping against it as well.

Though she continued to breathe hard, she'd regained at least some measure of control over her voice. She whimpered and groaned quietly as the aftershocks faded. Then, at last, she let out a satisfied moan.

"Good?" he asked, rather proud of himself. He then pressed his erection against her butt to quell its throbbing.

"Lord, honey," she answered, then chuckled. Her buttocks tensed, and she said, "You're still hard. You didn't come?"

He shook his head. A moment later he realized she couldn't see him and said, "No, I didn't come."

Diana Prince let out a pitiful whimper and said, "Oh lord. I don't know if I can take any more. Felt like you were splitting me in half. But it was soo good."

He had a thought almost immediately in response to that. "You could let me fuck those tits. I'd love to come all over them."

She gave a quick shake of her head, then took three fast, but deep breaths. She levered up on still wobbly arms, and looked back at him, revealing her face was flushed, and damp with sweat.

"Just do it," she said. "Fuck me and fill me up. Don't hold back. Fill me full of cum."

"Really?" he said, excited at the prospect of letting go inside her. No woman had ever let him do it before.

"Yes. Do it. Give it to me."

Grayson took his cock in hand, but the moment he pressed it against her folds, she winced.

"Are you sure?" he asked.

She answered not with words, but with action. She pushed back, taking him in and letting out a weepy whimper as he stretched her abused pussy.

"F-fill me up," she said again.

Half inside her hot, wet embrace, his reservations quickly faded, and he buried his cock to the hilt.

Diana yelped, the sound echoing back from the walls. She groaned as he pulled back, and then whimpered when his cock dove deep once more.

"Oh please, honey," she begged. "Do it. Come for me."

A low growl rumbled in his throat, and he slammed into her hard. Diana cried out, and then clamped her hand over her mouth once more.

surrendered to his lust, and fucked her with all he had. Ripples passed through her butt from the power of his thrusts, which jarred her forward. Her dark hair danced. She yelped and screeched into her hand. His thighs smacked loudly against her ass.

Knowing that he was going to come in her pussy aroused him to the extreme. In only a minute, the hot itch sprang up in the head of his cock, and spread down the shaft. His balls tightened. Barely controlled grunts and groans hummed in his throat as he rushed headlong toward orgasm.

The legs of the desk creaked. Stacks of paper shifted, and fluttered to the floor. Pens rolled off to thump atop them. The computer monitor wobbled despite its large, stable base. Grayson could feel her juices running through the wrinkles of his tight balls, and spattering against his thighs. Mindless of the potential consequences, his grunts of effort and ecstasy grew louder.

He was so intent on his pleasure that he was completely unprepared when hers rose to a crescendo.

Diana wailed into her hand as her pussy contracted around his fast-thrusting cock. Her other hand held onto the desk in a white-knuckled grip. Close to the edge himself, Dick Grayson instinctively dug his fingers into her hips, making sure he stayed inside her as she lurched and thrashed.

It didn't take long.

Somehow, he had the presence of mind to stop the primal roar that tried to rise up with his cum. He slammed into her, sending a final cascade of papers tumbling off the desk, and loosed a jet of hot cum inside her.

Dick's hips worked in jerky, uncontrolled bucks as her climaxing pussy milked his cock. Blast after blast of cum flooded her depths, until he was feeling light-headed. He continued to pulse long after he had nothing more to offer, and began to grow sensitive.

An especially strong squeeze of her walls was too much, and he jerked free. Without his cock buried inside her, and with his pants still entangling his shins, he lost his balance. He stumbled back, and his legs bumped into the chair. He sat down hard and grunted when the arm of the chair ended up squarely between his buttocks. A surge of effort plopped him into the seat, and he went limp.  
For some time, the only sound in the room was their heavy breathing, occasionally broken by a pained whimper from Diana. Grayson let his eyes flutter open, and had a perfect view of Diana's gaped pussy leaking his cum onto the floor. His sensitive cock protested mightily, and he snapped his eyes closed.

Diana muttered something, but he was to out of it to make out anything other than the honey at the end. He kept his eyes closed in post-come lethargy as he heard her moving around.

Eventually, he did open his eyes. Diana was sitting splay-legged on the desk in front of him, swabbing up the cum still dribbling from her with a wipe. The moment she noticed his eyes open, she dropped the wipe in the trash can next to the desk, and dipped her fingers into her pussy instead.

Dick Grayson stiffened and shivered as she tasted their mingled juices from her fingers, and moaned.

"You really filled me up, honey," she said while retrieving another wipe.

"Fuck," he groaned, still not completely recovered from the intensity of his orgasm.

"I know I'm going to regret it for a few days, but it was worth it. Good for you, honey?"

The smug look on her face said that she knew the answer from the amount of cum he'd blasted inside her, but he gave it anyway. He nodded his head, and said, "Oh yeah."

Diana spread her pussy lips, gave them a wipe, and when no more welled up, she slipped off the desk. He took a few wipes from the box she held out to him and steeled himself to clean up. He gasped from the first touch of the cold cloth, then got down to business. Diana knelt down in front of him, turning her attention to the mess on the floor.

She stood at about the same time he decided he'd accomplished all he could without a shower. Diana took the wipes from him, tossed them in the trash, and then finally pulled her blouse back down over her tits. After grabbing her purse, she reached out, ran her fingers through her hair, and said, "Need to go make myself presentable."

He grinned when she turned, flipped up her skirt, and gave her ass a spank before heading for the door. She peeked out, and then hurried into the hall.

Grayson looked at the mess they'd made of her desk, and the papers scattered all over the floor as he stood to pull up his pants. He chuckled, feeling a tingle between his legs as he remembered making that mess. The spontaneity, danger of discovery, and coming inside her bareback easily made it some of the best sex he'd ever had.

Dressed and fully recovered a little while later, he was thinking about heading out himself when Diana Prince returned. She'd fixed her hair, makeup, and settled her breasts properly in her blouse again.

"Do you think anybody heard?" he asked.

Diana Prince shook her head. "I think we're safe." She then walked over to her desk and retrieved her panties.

He made a quiet sound of approval as she stepped into them, and started to slide them up her legs. The sight was enough to start blood flowing back into his cock. Though it was a little numb, with a tinge of soreness, it just kept swelling. He had to reach down and adjust it as it hardened.

Diana smoothed out her skirt, and caught him pushing his hardening cock into a more comfortable position. "Are you getting hard again? Already?"

He shrugged and grinned.

Mrs Prince strutted over to him, and with no hesitation whatsoever, stooped down to see for herself. Her touch and her cleavage in his face hastened the process.

"Maybe we shouldn't have bothered getting dressed," he hinted, and grabbed a handful of her breast.

**Author's Note:**

> Comments are welcome.
> 
> Dick Grayson/Diana Prince Boss/Employee AU


End file.
